Diisopropylethylamine → (2R,5R)-2-(2,2-Dimethylpropoxy)-5-formylmorpholine-4-carboxylic acid tert-butyl ester

HRID 20358

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][OH:15])[CH2:12][O:11][C@@H:10]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.S(=O)(=O)=O.N1C=CC=CC=1>CS(C)=O.ClCCl>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH:14]=[O:15])[CH2:12][O:11][C@@H:10]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Dissolve (2R,5S)-2-(2,2-dimethylpropoxy)-5-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester (3.67 g, 12.1 mmol) in anyhydrous dimethylsulfoxide (25 mL) and dichloromethane (4 mL) and cool to 0° C. under nitrogen. Add diisopropylethylamine (7.4 mL, 42.3 mmol) then pyridine sulfur trioxide (3.47 g, 21.8 mmol) in 2 portions. Stir at 0° C. for 20 minutes and then remove from the cooling bath to allow all solids to dissolve. Pour into ice cold saturated aqueous sodium chloride, extract with 10% ethyl acetate/hexanes, wash with 0.1 N aqueous citric acid (30 mL), saturated aqueous sodium chloride (30 mL), dry (magnesium sulfate), filter and concentrate to give the desired compound as a colorless oil (3.37 g, 92%).

Aufarbeitung

customremove from the cooling bath
dissolutionto dissolve
additionPour into ice cold saturated aqueous sodium chloride
extractionextract with 10% ethyl acetate/hexanes
washwash with 0.1 N aqueous citric acid (30 mL), saturated aqueous sodium chloride (30 mL)
dry with materialdry (magnesium sulfate)
filtrationfilter
concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag: ord-467049d11563495c9cb444510d78b15a
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745438B2

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